diisopropyl-(1H,1H,2H,2H-perfluorodecyl)silyl triflate | 404942-40-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: diisopropyl-(1H,1H,2H,2H-perfluorodecyl)silyl triflate
• 英文别名: (F)TIPSOTf；[3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Heptadecafluorodecyl-di(propan-2-yl)silyl] trifluoromethanesulfonate
• CAS: 404942-40-1
• 化学式: C₁₇H₁₈F₂₀O₃SSi
• 分子量: 710.448
• InChiKey: DFOMMHUWTWHGJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.02
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  双丙酮半乳糖 、 diisopropyl-(1H,1H,2H,2H-perfluorodecyl)silyl triflate 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Heptadecafluoro-decyl)-diisopropyl-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-silane
  参考文献：
  名称：

  “Cap-Tag”—Novel Methods for the Rapid Purification of Oligosaccharides Prepared by Automated Solid-Phase Synthesis Financial support from the donors of the Petroleum Research Fund, administered by the ACS (ACS-PRF 34649-G1), Merck (Predoctoral Fellowship for E.R.P.), Boehringer-Ingelheim (Predoctoral Fellowship for E.R.P.), and the NIH (Biotechnology Training Grant for M.C.H.) is gratefully acknowledged. Funding for the MIT-DCIF Inova 501 was provided by the NSF (Award CHE-9808061). Funding for the MIT-DCIF Avance (DPX) 400 was provided by the NIH (Award 1S10RR13886-01). We thank Silicycle (Quebec City, Canada) for the generous gift of fluorous silica gel and isocyanate silica gel scavenger resin. We thank Dr. O. Plante for helpful discussions and help with the automated oligosaccharide synthesizer.

  摘要：

  DOI：

  10.1002/1521-3773(20011203)40:23<4433::aid-anie4433>3.0.co;2-8
• 作为产物：
  描述：

  三氟甲磺酸 、 (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)diisopropylsilane 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 diisopropyl-(1H,1H,2H,2H-perfluorodecyl)silyl triflate
  参考文献：
  名称：

  瓶盖标签固相寡糖合成

  摘要：

  一种新的“标签化”策略被应用于固相寡糖合成。乙酰基封端和荧光标记允许使用荧光固相萃取轻松地从乙酰基封端的缺失序列中分离所需的F标签寡糖。为了说明该方法，合成了保护的Glc-β-（1→6）-Man-α-（1→6）-Glc-β-1→戊烯基三糖。

  DOI：

  10.1021/jo701349c

文献信息

• Stereoselective Synthesis of Trisubstituted (<i>E</i>,<i>E</i>)-1,3-Dienes by the Site-Selective Reductive Cross-Coupling of Internal Alkynes with Terminal Alkynes: A Fragment Coupling Reaction for Natural Product Synthesis
  作者：Lark J. Perez、Heidi L. Shimp、Glenn C. Micalizio

  DOI：10.1021/jo901451c

  日期：2009.10.2

  olefinic coupling partners (vinyl halide or vinyl organometallic); it proceeds by a single convergent C−C bond-forming event (avoiding multistep methods based on carbonyl olefination) and is tolerant of a diverse array of functional groups including free hydroxyls. Through a systematic study of titanium-mediated reductive cross-coupling reactions of internal alkynes with terminal alkynes, a fragment

  描述了炔烃之间高度选择性的收敛偶联反应，用于合成立体定义的三取代（E，E）-1,3-二烯-通常在生物活性聚酮化合物衍生的天然产物的骨架中嵌入的结构基序。尽管存在许多合成该立体定义的官能团的多步骤方法，但是由于不需要立体定义的烯烃偶联伴侣（乙烯基卤化物或乙烯基有机金属），当前的方法代表了重大进步。它通过单个会聚的C-C键形成事件来进行（避免基于羰基烯化的多步方法），并且能够耐受包括游离羟基在内的多种官能团。通过对钛介导的内部炔烃与末端炔烃的还原性交叉偶联反应的系统研究，已经出现了在天然产物合成中非常有用的片段偶联反应。这里，在预先形成的钛环丙烯的官能化中使用近端羟基控制区域选择导致了高选择性双分子偶联过程的建立，其中CC键的形成与两个立体定义的烯烃的建立相一致。与已知的有关金属介导的偶联反应的文献相比，当前的工作定义了一项有力的进步，无需使用TMS-炔烃或共轭炔烃即可实现位点选择性双分子C-
• Comparison of the Relative Reactivities of the Triisopropylsilyl Group With Two Fluorous Analogs
  作者：Amador Garcia Sancho、Xiao Wang、Bin Sui、Dennis P. Curran

  DOI：10.1002/adsc.200900061

  日期：2009.5

  11,11,11-heptadeca-fluoroundecyl)silyl [C(8)F(17)(CH(2))(n)Si(i-Pr)(2), where n = 2 or 3], of the standard triisopropylsilyl (TIPS) group are compared in the setting of alcohol protection. The fluorous silyl groups can be installed under standard conditions in comparable yields to the TIPS group, but the derived fluorous silyl ethers are more labile than TIPS ethers towards cleavage by both acids and

  两种含氟类似物二异丙基（3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-十七氟癸基）甲硅烷基和二异丙基的相对稳定性- (4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-十七氟十一烷基)甲硅烷基[C(8)F(17)(标准三异丙基甲硅烷基 (TIPS) 基团的 CH(2))(n)Si(i-Pr)(2)，其中 n = 2 或 3]，在酒精保护设置中进行比较。氟甲硅烷基团可以在标准条件下以与 TIPS 基团相当的产率安装，但衍生的氟甲硅烷基醚比 TIPS 醚更容易被酸和氟化物裂解。
• Fluorous TBAF: A Convenient and Selective Reagent for Fluoride-Mediated Deprotections
  作者：Santos Fustero、Amador García Sancho、José Luis Aceña、Juan F. Sanz-Cervera

  DOI：10.1021/jo901245m

  日期：2009.8.21

  A fluorous analogue of TBAF has been developed for its use in the clean removal of silicon-derived protecting groups. Purification of the crude mixtures by fluorous solid-phase extractions allowed alcohols, amines, and carboxylic acids to be obtained in high purity, with no need of chromatographic separations. The moderate reactivity of fluorous TBAF was exploited in selective deprotections of several bifunctional molecules.
• Confirmation of the Stereostructure of (+)-Cytostatin by Fluorous Mixture Synthesis of Four Candidate Stereoisomers
  作者：Won-Hyuk Jung、Sabrina Guyenne、Concepción Riesco-Fagundo、John Mancuso、Shuichi Nakamura、Dennis P. Curran

  DOI：10.1002/anie.200704893

  日期：2008.1.25
• “Cap-Tag”—Novel Methods for the Rapid Purification of Oligosaccharides Prepared by Automated Solid-Phase Synthesis Financial support from the donors of the Petroleum Research Fund, administered by the ACS (ACS-PRF 34649-G1), Merck (Predoctoral Fellowship for E.R.P.), Boehringer-Ingelheim (Predoctoral Fellowship for E.R.P.), and the NIH (Biotechnology Training Grant for M.C.H.) is gratefully acknowledged. Funding for the MIT-DCIF Inova 501 was provided by the NSF (Award CHE-9808061). Funding for the MIT-DCIF Avance (DPX) 400 was provided by the NIH (Award 1S10RR13886-01). We thank Silicycle (Quebec City, Canada) for the generous gift of fluorous silica gel and isocyanate silica gel scavenger resin. We thank Dr. O. Plante for helpful discussions and help with the automated oligosaccharide synthesizer.
  作者：Emma R. Palmacci、Michael C. Hewitt、Peter H. Seeberger

  DOI：10.1002/1521-3773(20011203)40:23<4433::aid-anie4433>3.0.co;2-8

  日期：2001.12.3